Acetic Acid → 1-(4-Boc-aminobutyl)piperazine

HRID 1097298Notes

Reaction equation

HRID 1097298 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.C(O)(=O)C>CO.[OH-].[OH-].[Pd+2]>[C:25]([O:24][C:22](=[O:23])[NH:21][CH2:20][CH2:19][CH2:18][CH2:17][N:14]1[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1)([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 59708788HCID 59708788, compound

Product 1

HCID 41346911-(4-Boc-aminobutyl)piperazineYield 91%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-(4-tert-butoxycarbonylaminobutyl)piperazine-1-carboxylic acid benzyl ester (16) (3.26 g, 8.33 mmol), acetic acid (0.5 mL), and palladium hydroxide on carbon (60% wet, 0.98 g) in methanol (15 mL) was stirred under atmospheric hydrogen for 16 h. The catalyst was removed by suction filtration over Celite. The filtrate was concentrated in vacuo and the resulting residue was purified by Biotage silica gel column chromatography using concentrated ammonium hydroxide/methanol/dichloromethane to give 17 as a yellow oil (1.94 g, 91% yield): 1H NMR (300 MHz, CDCl3) δ 1.44 (s, 9H), 1.53 (m, 4H), 2.35 (m, 6H), 2.45 (br, 1H), 2.94 (t, 4H), 3.12 (m, 2H), 5.32 (br, 1H); ESI MS m/z 258 [C13H27N3O2+H]+.

Workup

  1. customThe catalyst was removed by suction filtration over Celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe resulting residue was purified by Biotage silica gel column chromatography

Sources & evidence

ORD record
ord-113925ec462a4b68b1396b0c3646ebc4
Source dataset
uspto-grants-2012_03
Patent number
US08143256B2

Reaction notes

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